Robert O. Caulfield

American Landscape Artist Robert Owen Caulfield, 1930-2025

A fine artist who achieved spectacular success after age fifty-five, Robert O. Caulfield died on November twentieth in Nashua, New Hampshire. Twenty-four days shy of what would have been his ninety-fifth birthday.

Born in the Boston Lying-In Hospital for the poor in December 1930, Robert’s childhood played out on the crime-ridden desperate streets of the Roxbury district.

A top ten hit in 1931, “Life is Just a Bowl of Cherries” in no way reflected Robert’s early years. The love that linked his mother and father’s union died, if it had ever existed at all. The repercussions of that laid heavily on both their sons.

Robert’s parents’ 1937 separation resulted in he and his one-year-older brother Joseph being entrusted to the care of their tipsy maternal grandmother.

Home was now a hovel crawling with cats and whiskey bottles. Like his former home in a shabby apartment above the Roxy Theater a few blocks away, neglect and indifference were all that could be counted on under that roof.

Running wild on the city streets, Robert grew adept at avoiding truant officers. Over the next four years, too many weekdays to mention were to pass without him hearing a school bell.

Setting foot off his block meant a potential fistfight any day of the week. Robert never backed down and rarely lost a battle. He became an adept food thief to supplement his at-home diet of mustard sandwiches or a slice of a Mars bar.

A gifted natural athlete, Robert was welcome on any playing field, be it a pick-up game on the street or a school team.

He was required to repeat a grade one year when his days ditching school far exceeded his days in attendance. As much as he excelled at baseball, football was Robert’s game.

A family court appearance in April of 1941resulted in Robert and his brother finding neither their mother nor father requested custody of either of them.

Long unhappy with her grandsons’ squalid living conditions, Robert’s paternal grandmother and her husband secured permanent custody of both boys.

Some adolescents find drawing and coloring an enjoyable pastime. For Robert, creativity was not a pursuit. He was channeling his soul. During grade school art lessons, Robert’s intuitive sense of how to craft a painting, and how to mix colors, enhanced his developing skills as a sketch artist and painter.

After years of waking up in a boozy Roxbury slum, Robert now opened his eyes each morning in a tidy middle-class home in east Lynn, on Boston’s North Shore. Although never an eager student, Robert began showing up for class at the local parochial school.

A set of oil paints and some canvas boards lay among the presents lying under the tree for him his first Christmas morning in Lynn. Although his father remained a shadow figure on the edge of his life, Robert never saw his mother again.

Throughout World War II, Robert scoured each new issue of LOOK or LIFE for the work of the artists defining that conflict’s events, like Ogden Pleissner and Reginald Marsh. He spent countless hours copying the Sunday comic strips and the work of sports page illustrators. Disney cartoon characters, too.

Robert’s spectacular accomplishments playing halfback for the Lynn English High School Bulldogs resulted in offers of full athletic scholarships from Harvard University and Holy Cross.

Despite the all-scholastic athletic status he attained, Robert considered his poor background too insurmountable a social barrier to entering an upper-class collegiate environment.

He declined all offers. He did not think he was good enough. Besides. He had fallen in love with an extraordinary girl named Marilyn.

During a stint in the Marine Corps in 1950, Robert stepped into a Hollywood bookstore and picked up a copy of Irving Stone’s biographical novel about Vincent van Gogh. Lust for Life introduced him to a man whose life defines the artistic quest.

The Impressionist artistic movement Van Gogh so exemplified left a lifelong influence on Robert. Books on Monet, Renoir, Degas, and Sisley soon joined his growing art book collection. Most of all, Camille Pissarro’s work and philosophy influenced Robert’s developing style as a landscape artist.

At the age of twenty-one, Robert hitch-hiked cross-country after mustering out of the Marine Corps. He bought a used car with his separation pay, instead of the refrigerator his grandmother, who still used an icebox, dreamed of owning. Robert regretted that decision for the rest of his life.

Once back east, he talked Marilyn, “The Sweetheart of Lynn English High” into eloping. One year and a half after she had sent him a “Dear John” letter when he was in the service. The couple’s decision to run away was prompted by Robert’s parish priest’s aversion to a union in which Robert’s Protestant intended would not convert to Catholicism.

Robert and Marilyn began married life together on the third floor of a triple-decker that her parents owned and resided two floors below in, on Boston Street in Lynn. Rent and utility bills were not going to wait for artistic glory to shower money and acclaim on Robert. By the time his first son was born in 1953, he had found a solid union job as a truck driver for the Lynn Gas and Electric Company.

Galleries in the coastal art colony of nearby Rockport proved reluctant to represent the work of a non-academic painter who had not apprenticed or studied in a formal environment.

Displaying his paintings in local banks, retail establishments, and restaurants, Robert averaged five or six sales per year.

Editors of art magazines, as well as LIFE, LOOK, and The New Yorker received letters and photos of Robert’s latest paintings from him on a regular basis.

Robert followed art movements like Abstract Expressionism and Pop Art with interest, but drew his inspiration from traditional subject matter, like the landscapes of John Sloan and Alfred Sisley. His sincere belief was that every painting was ultimately abstract, and that the artist must aim to evoke emotion in the viewer, just as a musician would strive to do in a great song.

Robert quit his night-school studies at the Practical School of Art in Boston when his growing family put the kibosh on that expenditure. In 1958, he joined a group of other local artists in opening the Coronet Art Gallery in Lynn. He was one of the few artists who sold some paintings during the gallery’s six months in business.

In 1961, the American realist painter Edward Hopper chose Robert’s painting, “Nuns on a Misty Morning” as one of the “Best in Show” at the annual art exhibition sponsored by Boston’s Jordan Marsh department store. That painting was also one of the few that sold that year.

By 1965, Robert and Marilyn’s family had expanded to five children. The couple moved to a four-bedroom, nineteenth-century house in suburban Lynnfield.

Despite his responsibilities as a husband, provider, and father, the flames of Robert’s artistic drive still burned. Yet there were periods when working sixty-hour weeks at the gas company reduced that fire to a pilot light.

The most critical element for creation in any artist’s life is time. Robert suddenly had so little of it that his output slowed to four or five paintings per year. His landscapes from the 1960s and 1970s appeared on the national calendar produced by the American Mutual Insurance Company frequently during this period.

His devotion to his job found Robert rising through the ranks at Lynn Gas. Working foreman. Foreman. Manager by the Summer of Love, in 1967.

Robert was chosen over numerous college-educated candidates to become the Boston Gas Company’s District Supervisor of Boston’s North Shore a few years later. Strictly on his impeccable work record alone.

During his thirty-five-year career with Lynn Gas, (and the Boston Gas Company, following a merger), the only time Robert ever missed a day’s work was during his recuperation from a gas explosion.

A series of Beacon Hill landscapes Robert painted led to an invitation to join the prestigious Copley Society of Art in Boston in the early 1970s. By 1975, age forty-five, Robert had achieved the American Dream by any measure, right down to the built-in swimming pool in his backyard.

He walked to Lynn to get to work during the period the Blizzard of 1978 closed all north shore roads for almost two weeks.

Despite his material success, in Robert’s own eyes he was a failure. The goal that had consumed him since childhood—recognition as a landscape artist—had proven elusive. In spite of the considerable effort he had devoted to his craft and promoting his artwork.

One of Robert’s promotional letters resulted in his painting, “Stowe, Vermont” appearing in the centerspread of the October issue of Yankee magazine in 1982. The public response to the Stowe painting prompted Marilyn to reiterate the time had come for her husband to focus on painting full-time.

Two years later, Robert and Marilyn took early retirement. With no business plan but a dream, they opened the Robert O. Caulfield Art Gallery in Woodstock, Vermont.

Although Robert sold a painting the day the gallery opened, the first couple years his gallery’s doors were open proved touch and go, in terms of sales.

Beginning in 1987, Marilyn and her formidable sales skills became more involved in that part of the business. Robert went on to average one-hundred original oil paintings and watercolors sold each year for the next thirty-two years.

In 2001, Robert and Marilyn moved up the street to a brick mansion at 11 The Green, on Woodstock’s village green.

Over the thirty-five years the Caulfield Art Gallery was in operation, Marilyn and Robert sold over three thousand of his original oil paintings and watercolors. Hundreds of lithographs and sketches, as well.

In terms of family, those thirty-five years included the birth of one grandchild after another, anniversaries, weddings, and so much joy that Robert sometimes wondered if he had stepped into someone else’s life.

Coupling his extraordinary drive with a profound work ethic, the unwanted kid from Roxbury went on to become one of the best-selling artists in the world.

Robert and Marilyn spent the past two decades of their lives living in one of the finest mansions in Woodstock, Vermont. Winter breaks were spent at their Florida condominium or traveling the world.

Shortly before Marilyn’s death in 2019, Robert closed his Woodstock art gallery at the age of eighty-eight.

Although the world was not kind to the child he had once been, Robert fought to turn his luck around and become the man he dreamed he could be.

He is survived by his five children, thirteen grandchildren, and thirteen great-grandchildren.

A favorite quote of Roberts by Camille Pissarro stated: “It is only in the long run that I aim to please . . . but the eye of the passerby is too hasty and sees only the surface. Those in a hurry will not stop for me.”

His Funeral Mass will be celebrated in Saint Maria Goretti Church, 112 Chestnut Street, Lynnfield on Monday, December 1 at 11am. Visitation will be held in the church prior to the mass from 10am-11am. Interment, with military honors, will follow the mass at Forest Hill Cemetery, Lynnfield. Arrangements are in the care of the McDonald Funeral Home, Wakefield. 

At his request, any donations on Robert’s behalf should be made to St. Jude’s Children’s Hospital in Memphis, Tennessee.